Lycorine chloride

Names

[ Name ]:
Lycorine chloride

[Synonym ]:
Lycorine hydrochloride
Lycorinehydrochloride
Licorin hydrochloride
galanthidine,hydrochloride
(1S,2S,12bS,12cS)-2,4,5,7,12b,12c-Hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol hydrochloride (1:1)
1H-[1,3]Dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol, 2,4,5,7,12b,12c-hexahydro-, (1S,2S,12bS,12cS)-, hydrochloride (1:1)
Lycorinechloride
Lycorine (hydrochloride)

Biological Activity

[Description]:

Lycorine (hydrochloride) is VE-cadherin inhibitor,and has IC50 of 1.2μM in Hey1B cell.IC50: 1.2μM (Hey1B cell)[2]In vitro:Lycorine (hydrochloride) executed an anti-melanoma vasculogenic effect by inhibiting VE-cadherin gene expression in C8161 cells and caused a decrease in cell surface exposure of VE-cadherin protein. Consistently, LH significantly suppressed VE-cadherin gene promoter activity. [1]Lycorine (hydrochloride) effectively inhibited mitotic proliferation of Hey1B cells (half maximal inhibitory concentration = 1.2 μM) with very low toxicity, resulting in cell cycle arrest at the G2/M transition through enhanced expression of the cell cycle inhibitor p21 and marked down-regulation of cyclin D3 expression. Moreover, LH suppressed both the formation of capillary-like tubes by Hey1B cells cultured in vitro.[2]In vivo: Lycorine effectively suppressed C8161 cell-dominant tumor formation and generation of tumor blood vessels in vivo with low toxicity.[1]Lycorine (hydrochloride) suppressed the formation of the ovarian cancer cell-dominant neovascularization in vivo when administered to Hey1B-xenotransplanted mice, suggest that LH selectively inhibits ovarian cancer cell proliferation and neovascularization and is a potential drug candidate for anti-ovarian cancer therapy.[2]

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Natural Products >> Alkaloid

Research Areas >> Cancer

[References]

[1]. Liu, R. et al. Lycorine hydrochloride inhibits metastatic melanoma cell-dominant vasculogenic mimicry. Pigment cell & melanoma research 25, 630-638, doi:10.1111/j.1755-148X.2012.01036.x (2012).

[2]. Cao, Z. et al.Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity. Toxicology letters 218, 174-185, doi:10.1016/j.toxlet.2013.01.018 (2013).

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
477.4ºC at 760 mmHg

[ Melting Point ]:
210-212ºC

[ Molecular Formula ]:
C₁₆H₁₈ClNO₄

[ Molecular Weight ]:
323.77

[ Flash Point ]:
242.5ºC

[ PSA ]:
62.16000

[ LogP ]:
0.68650

[ Vapour Pressure ]:
6.37E-10mmHg at 25°C

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OL2910000

CHEMICAL NAME :: Lycoran-1-alpha,2-beta-diol, 3,3-alpha-didehydro-, hydrochloride

CAS REGISTRY NUMBER :: 2188-68-3

LAST UPDATED :: 198803

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C16-H17-N-O4.Cl-H

MOLECULAR WEIGHT :: 323.80

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 230 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 54,21,1958

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 117 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 54,21,1958

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 123 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - nausea or vomiting

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 54,21,1958

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
45

[ RIDADR ]:
UN 2811

[ Hazard Class ]:
6.1

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